A facile route towards new chitin derivatives with both catalytical and biological activities is proposed in the course of methodology development aimed at the design of polyfunctional materials on the basis of renewable and accessible natural polysaccharides. Ultrasound-promoted and Cu(I)-catalyzed azido-alkyne click cycloaddition of the propargylic ester of nicotinic acid and its N-methylated analogue to the azido chitin derivative allowed us to obtain previously unknown non-toxic water-soluble derivatives of chitin. The obtained polymers and their based nanoparticles demonstrated a high antibacterial activity in vitro, which is comparable or even superior to that of commercial antibiotics ampicillin and gentamicin. New derivatives of chitin were also shown to be highly efficient and reusable (at least for 10 times) green catalysts for the aldol reaction in water. The catalysts can be easily separated from the reaction mixture by their precipitation with ethanol. The results obtained highlight prospects of further studies on chitin's application in the rational design of novel functional materials with valuable properties. © 2020 Elsevier B.V.